EP1145710A1 - Verwendung von Ascorbinsäurederivaten, um die Synthese von epidermalen Ceramiden zu erhöhen - Google Patents

Verwendung von Ascorbinsäurederivaten, um die Synthese von epidermalen Ceramiden zu erhöhen Download PDF

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Publication number
EP1145710A1
EP1145710A1 EP01400781A EP01400781A EP1145710A1 EP 1145710 A1 EP1145710 A1 EP 1145710A1 EP 01400781 A EP01400781 A EP 01400781A EP 01400781 A EP01400781 A EP 01400781A EP 1145710 A1 EP1145710 A1 EP 1145710A1
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EP
European Patent Office
Prior art keywords
radical
ascorbic acid
use according
group
isopropylidene
Prior art date
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Granted
Application number
EP01400781A
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English (en)
French (fr)
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EP1145710B1 (de
Inventor
Isabelle Castiel
Corinne Ferraris
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LOreal SA
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LOreal SA
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Publication date
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Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the invention relates to the use of certain ascorbic acid derivatives for the manufacture of a composition intended to increase the synthesis of epidermal ceramides.
  • Human skin consists of two compartments, namely a deep compartment, the dermis, and a superficial compartment, the epidermis.
  • the dermis provides the epidermis with solid support. It is also its nourishing element. It is mainly consisting of fibroblasts and a compound extracellular matrix itself mainly collagen, elastin and a substance, called the fundamental substance, components synthesized by the fibroblast. There are also leukocytes, mast cells or tissue macrophages. It also contains blood vessels and nerve fibers.
  • the epidermis is in contact with the external environment. Its role is to protect the body of dehydration and external aggressions, whether chemical, mechanical, physical or infectious.
  • the natural human epidermis is mainly composed of three types of cells which are the keratinocytes, very predominant, melanocytes and Langerhans cells. Each of these cell types contribute by their own functions to the essential role played in the body through the skin.
  • the cells constituting the epidermis are delimited by a lipid domain.
  • phospholipids whose role is to develop the fluid structure of cell membranes of the living layers of the epidermis, are gradually replaced by a mixture composed mainly of fatty acids, cholesterol and sphingolipids.
  • lipids are organized into specific lamellar structures whose integrity does not depend only the quality of the fractions present but also their respective proportion. This lamellar structure of lipids in the lipid domain of the epidermis is responsible for the fluidity therefore of the suppleness of the skin.
  • Lipids are also responsible for the "barrier" properties of the epidermis particularly the stratum corneum.
  • Epidermal lipids are synthesized mainly in the living epidermis. They are mainly consisting of phospholipids, sphingolipids, cholesterol, fatty acids free, triglycerides, cholesterol esters and alkanes.
  • Phospholipids are essential for the constitution of cell membranes. They play an important role in the mediation of extracellular signals and the formation of chains free aliphatics used for energy production. They constitute a reservoir of acids free fat necessary for the constitution of sphingolipids.
  • Sphingolipids are essential for maintaining the structure multilamellar intercoreeocytic lipids. They are also essential for water exchanges and the "barrier" function of the epidermis.
  • Cholesterol plays a key role in skin hydration and in the "barrier" function of the epidermis.
  • Free fatty acids play a major role in maintaining the lamellar structure of stratum corneum lipids, as well as in the constitution of cell membranes where they are responsible for membrane fluidity but also for physiological processes such as the functioning of receptors or enzyme activity.
  • the human epidermis has changes in its composition and / or lipid synthesis.
  • vitamin C derivatives which are more stable than acid ascorbic itself.
  • application EP-0 664 290 describes mono- and diesters of acid cinnamic acid or one of its derivatives with ascorbic acid or a derivative. These compounds can be used as antioxidants in cosmetic compositions or pharmaceutical products, in particular to protect the lipids of the skin against oxidation induced by free radicals.
  • Ascorbic acid derivatives which are esters of (5,6-isopropylidene) ascorbyl, are described in applications JP-46 024 699 and JP-44 000 220.
  • ascorbic acid such as the acid 2-O- ⁇ -D glucopyranosyl L-ascorbic (or ascorbyl glucoside)
  • ascorbyl glucoside are commercially available.
  • Glucoside ascorbyle is used in particular as a depigmenting agent.
  • the group R 1 is chosen in such a way that the bond R 1 O is easily hydrolyzable in contact with the skin.
  • sugar residue is preferably meant a residue of glucose, galactose, mannose, fructose or N-acetylglucosamine.
  • saturated, linear or branched hydrocarbon radical having from 1 to 20 carbon atoms it is includes, for example, a radical chosen from the group consisting of methyl radicals, ethyl, propyl, iso-propyl, butyl, iso-butyl, tert-butyl, hexyl, heptyl, 2-ethyl-hexyl, octyl, nonyl, iso-nonyl, decyl, undecyl, dodecyl, pentadecyl, hexadecyl and octadecyl, and preferably the undecyl radical.
  • linear or branched unsaturated hydrocarbon radical having from 1 to 20 atoms of carbon means more particularly a radical chosen from the group consisting of radicals containing from 2 to 5 carbon atoms and having one or more unsaturations ethylenic, in particular the allyl radical.
  • the preferred or substituted aryl radical is the benzyl radical
  • aralkyl radicals corresponding to formula (II) above are those in which the aryl group is substituted by: one or more hydroxy radicals; alkoxy such a radical chosen from the group consisting of methoxy, ethoxy and butoxy radicals, and preferably the methoxy radical; fluoroalkoxy such as the trifluoromethoxy radical; and alkylcarbonyloxy such as a radical chosen from the group consisting of acetoxy radicals, propionyloxy and butyryloxy, and preferably acetoxy.
  • Ascorbyl (5,6-isopropylidene) 2-hexadecanoate and (5,6-isopropylidene) 2-benzoate ascorbyle are particularly preferred.
  • compositions generally comprising a physiologically acceptable medium.
  • This composition advantageously contains from 0.001 to 10% by weight, and preferably from 0.01 at 1% by weight, of ascorbic acid derivative.
  • ceramides increase the synthesis of ceramides epidermal.
  • ceramides is meant, according to the present description, also well the ceramides of type I to VII, in particular the ceramides of type IV to VII, that the acylglucosylceramides.
  • composition containing them particularly well suited to improving the function skin barrier, which in turn allows better water retention in the skin.
  • the ascorbic acid derivatives mentioned above can thus be used in a composition moisturizing cosmetic, and the resulting composition in a cosmetic process of hydration of the skin, comprising the application to the skin of this composition.
  • the ascorbic acid derivatives according to the invention can be used for cosmetic purposes, as agents to improve the suppleness of the skin and / or the surface appearance of the skin (manifested in particular by roughness and the presence wrinkles and fine lines) and / or fight against or prevent intrinsic aging of the skin. They can also be useful to protect the skin against attacks, in particular against the effects of chemicals such as surfactants, substances irritating cosmetics such as retinoids, physical aggression such as friction, and also against the effects of cold or wind.
  • chemicals such as surfactants, substances irritating cosmetics such as retinoids, physical aggression such as friction, and also against the effects of cold or wind.
  • composition according to the invention can also be used to manufacture a preparation intended to improve the barrier function of the skin.
  • a preparation can be intended to the treatment of certain pathologies involving a disturbance of the barrier function, such as atopic or seborrheic dermatitis.
  • the ascorbic acid derivatives mentioned above can be used to improve the lipid content and / or the barrier function of the reconstructed epidermis.
  • the addition of at least one of these derivatives in the culture medium of the reconstructed epidermis thus makes it possible to bring these epidermis closer to the structure of normal human skin and, by the same token, to make the tests in vitro (in particular the studies penetration) performed on these epidermis which are more predictive of the phenomena that will be observed in vivo.
  • composition of the invention can be in all dosage forms normally used for topical application, especially in the form of a solution aqueous, hydroalcoholic or oily, of an oil-in-water or water-in-oil emulsion or multiple, an aqueous or oily gel, a liquid, pasty or solid anhydrous product, a dispersion of oil in an aqueous phase using spherules, these spherules can be polymeric nanoparticles such as nanospheres and nanocapsules or, better, lipid vesicles of ionic and / or nonionic type.
  • This composition can be more or less fluid and have the appearance of a white cream or colored, an ointment, a milk, a lotion, a serum, a paste, a foam. She can optionally be applied to the skin as an aerosol. It can also be present in solid form, in particular in the form of a lip stick when it is for example intended to treat lip cracks. It can be used as a product of care and / or as a make-up product for the skin.
  • the composition of the invention may also contain adjuvants usual in the cosmetic field, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, fragrances, fillers, filters, pigments, odor absorbers and materials coloring
  • adjuvants usual in the cosmetic field, such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, fragrances, fillers, filters, pigments, odor absorbers and materials coloring
  • the quantities of these various adjuvants are those conventionally used in the field considered, and for example from 0.01 to 20% of the total weight of the composition.
  • These adjuvants depending on their nature, can be introduced into the fatty phase, into the aqueous, in lipid vesicles and / or in nanoparticles. In any case, these adjuvants, as well as their proportions, will be chosen so as not to harm the desired properties of the combination of active agents according to the
  • the proportion of the fatty phase can range from 5 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition:
  • the oils, emulsifiers and coemulsifiers used in the composition in the form of an emulsion are chosen from those conventionally used in the domain considered.
  • the emulsifier and the coemulsifier are present in the composition, in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight, per relative to the total weight of the composition.
  • oils which can be used in the invention mention may be made of mineral oils ( petroleum jelly), oils of vegetable origin (avocado oil, soybean oil), oils of origin animal (lanolin), synthetic oils (perhydrosqualene), silicone oils (cyclomethicone) and fluorinated oils (perfluoropolyethers).
  • mineral oils petroleum jelly
  • oils of vegetable origin oils of vegetable origin
  • lanolin oils of origin animal
  • synthetic oils perhydrosqualene
  • silicone oils cyclomethicone
  • fluorinated oils perfluoropolyethers
  • fatty alcohols cetyl alcohol
  • fatty acids fatty acids
  • waxes waxes (wax carnauba, ozokerite).
  • emulsifiers and coemulsifiers which can be used in the invention, mention may be made of: for example fatty acid and polyethylene glycol esters such as PEG-20 stearate, and fatty acid and glycerin esters such as glyceryl stearate.
  • hydrophilic gelling agents mention may in particular be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as acrylate / alkylacrylate copolymers, polyacrylamides, polysaccharides, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, salts metallic fatty acids, hydrophobic silica and polyethylenes.
  • keratolytic agents and / or scaling agents can be used, depigmenting agents, UV filters, anti-free radical agents and mixtures thereof.
  • depigmenting agents As active agents, keratolytic agents and / or scaling agents can be used, depigmenting agents, UV filters, anti-free radical agents and mixtures thereof.
  • at least some of the assets may be incorporated into spherules, in particular ionic or nonionic vesicles and / or nanoparticles (nanocapsules and / or nanospheres), so that the active ingredients which are incompatible with each other are isolated from each other in the composition.
  • the ascorbyl glucoside and the ascorbic acid itself are tested on an equivalent of skin sold by EPISKIN (LYON, France), after culturing it for 7 days.
  • the culture and test media are those included in the kit sold by the supplier.
  • Each compound was tested at 5 ⁇ g / ml and 0.05 ⁇ g / ml (in vitamin C equivalent) in the culture centre.
  • the reconstructed epidermis is treated for five days, the middle of culture being renewed every 48 hours.
  • the witness consists of an equivalent identical epidermis undergoing topical application of culture medium without compound to test.
  • the epidermis equivalent is detached from its collagen support.
  • the preparation of the lipids of the epidermis equivalent, and their analysis by HPTLC or high performance thin layer chromatography, are performed according to the technique and with the pads described by M. Ponec (1991, Adv. Lipid Res. 24: 83-117).
  • densitometric analysis is carried out using a densitometric reader CAMAG TLC, Scanner 3 model.
  • Example 1 The test described in Example 1 was repeated using different ascorbic acid derivatives, applied for 6 days at 1.10 ⁇ 10 -4 M on reconstructed epidermis subjected to 7 days of culture. However, the quantity of epidermal ceramides produced has not been quantified. Instead, a densitometric analysis was performed using a CAMAG TLC® Model Scanner 3 densitometric reader.
  • Compound E is described, as well as its method of preparation, in application JP-07 206 840.
  • Compound F is commercially available from SIGMA.
  • the figure represents the lipid content of the reconstructed epidermis sample being untreated (control), either treated with ascorbic acid (vit C) or with one of the ascorbic acid derivatives A to G above.
  • the area framed in this figure corresponds to polar ceramides (ceramides IV to VII).
  • composition is prepared in a conventional manner: Octyldodecanol 0.2% Cyclomethicone 5% Dimethicone copolyol 5% Tocopheryl acetate 1% UV filter 1% Ascorbyle glucoside 0.1% Glycerin 3% Disodium EDTA 0.1% PH adjusters 2.6% Preservatives 0.4% Gelling agents 1.2% Water qs. 100%
  • a fluid is obtained which can be applied morning and / or evening to the face to improve the suppleness of the skin and smooth wrinkles and fine lines.
  • An oil-in-water type emulsion is prepared by mixing the following ingredients: Ascorbyle 2-cinnamate 0.1% Polyethylene glycol oxyethylenated to 50 moles of EO 3% Mono stearate diglycerol 3% Vaseline oil 24% Cetyl alcohol 5% Water qs 100%
  • a cream is obtained which can be applied morning and / or evening to the face to improve the suppleness of the skin and smooth wrinkles and fine lines.
  • composition is prepared by mixing the following ingredients: 2- ascorbyle ferulate 0.1% Jojoba oil 13% Mixture of methyl and propyl paraben 0.05% Potassium sorbate 0.3% Cyclopentadimethylsiloxane 10% Stearyl alcohol 1% Stearic acid 4% Polyethylene glycol stearate 3% Glycerol 3% Water qs 100%
  • a cream is obtained which is well suited for the treatment of dry skin.
  • ascorbyle 2-ferulate can be replaced by the same amount of 2-ferulate of (5,6-isopropylidene) ascorbyl or of 2- (4-actéoxyférulate) of (5,6-isopropylidene) ascorbyle.
  • An oil-in-water type emulsion is prepared by mixing the following ingredients: (5,6-isopropylidene) ascorbyl 2-hexadecanoate 0.1% Octyl palmitate 10% Glycerol mono-isostearate 4% Vaseline oil 24% Vitamin E 1% Glycerol 3% Water qs 100%
  • a cream is obtained which can be applied morning and / or evening to the face to improve the suppleness of the skin and smooth wrinkles and fine lines.
  • 2-benzoate of (5,6-isopropylidene) ascorbyl may be substituted for 2-hexadecanoate of (5,6-isopropylidene) ascorbyle.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Toxicology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP01400781A 2000-04-10 2001-03-27 Verwendung von Ascorbinsäurederivaten, um die Synthese von epidermalen Ceramiden zu erhöhen Expired - Lifetime EP1145710B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0004574 2000-04-10
FR0004574A FR2807320B1 (fr) 2000-04-10 2000-04-10 Utilisation de derives d'acide ascorbique pour augmenter la synthese des creramides epidermiques

Publications (2)

Publication Number Publication Date
EP1145710A1 true EP1145710A1 (de) 2001-10-17
EP1145710B1 EP1145710B1 (de) 2006-11-02

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EP01400781A Expired - Lifetime EP1145710B1 (de) 2000-04-10 2001-03-27 Verwendung von Ascorbinsäurederivaten, um die Synthese von epidermalen Ceramiden zu erhöhen

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US (2) US20020042380A1 (de)
EP (1) EP1145710B1 (de)
JP (2) JP2001316261A (de)
AT (1) ATE344016T1 (de)
DE (1) DE60124170T2 (de)
ES (1) ES2273789T3 (de)
FR (1) FR2807320B1 (de)

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EP1192938A2 (de) * 2000-09-29 2002-04-03 JOHNSON & JOHNSON CONSUMER COMPANIES, INC. Zusammensetzung zur Verbesserung der Permeation von topischen Hautpflegemitteln
FR2825922A1 (fr) * 2001-06-15 2002-12-20 Oreal 2-hexadecanoate d'ascorbyle comme inhibiteur de no-synthase et utilisations
EP1374850A1 (de) * 2002-06-20 2004-01-02 L'oreal Kosmetische und/oder dermatologische Verwendung einer Zusammensetzung, die mindestens einen oxidationsempfindlichen hydrophilen durch mindestens einem Polymer oder Copolymer stabilisierten Wirkstoff aus Maleinsäureanhydrid enthält
EP1430883A1 (de) * 2002-12-18 2004-06-23 L'oreal Kosmetische Vewendung von Ascorbinsäurederivaten als Haut- oder Haar-Aufheller
EP1442739A1 (de) * 2003-02-03 2004-08-04 L'oreal Verwendung von Zimtsäure mono- und di-Estern oder von Derivaten und Vitamin C, als NO Donor
FR2850579A1 (fr) * 2003-02-03 2004-08-06 Oreal Utilisation de mono-ou di-esters d'acide cinnamique ou de l'un de ses derives et de vitamine c, comme donneur de no
FR2855047A1 (fr) * 2003-05-19 2004-11-26 Oreal Composition comprenant une base sphingoide, un activateur de la voie des 4-et/ou des 6-hydroxylases et un acide gras, utilisation pour renforcer la fonction barriere de la peau
EP1527777A1 (de) * 2003-10-31 2005-05-04 MERCK PATENT GmbH Zubereitung mit antioxidanten Eigenschaften, die einen Benzoesäureester der Ascorbinsäure enthält
EP1620419A2 (de) * 2003-04-21 2006-02-01 Tagra Biiotechnologies Ltd. Stabilisierte ascorbinsäurederivative
EP2204163A1 (de) 2008-12-30 2010-07-07 L'oreal Kombination aus Monosaccharide und Ascorbinsäure und ihre kosmetische Verwendung
WO2010142663A1 (fr) * 2009-06-08 2010-12-16 Pierre Fabre Dermo-Cosmetique Mono esters et bis esters d'acide gras insature sur l'acide ascorbique et leurs utilisations cosmetiques
US8039026B1 (en) 1997-07-28 2011-10-18 Johnson & Johnson Consumer Companies, Inc Methods for treating skin pigmentation
WO2013021105A2 (fr) 2011-08-11 2013-02-14 Ascorbix Sarl Nouveaux dérivés de furanones et composition pharmaceutique les contenant
EP1842522A4 (de) * 2004-12-28 2015-07-08 Otsuka Pharma Co Ltd Feste öl-in-wasser-emulsion

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US20020006418A1 (en) * 1998-10-13 2002-01-17 John Kung Composition to enhance permeation of topical skin agents
US20020197244A1 (en) * 1998-12-07 2002-12-26 Miri Seiberg Compositions and methods for regulating phagocytosis and ICAM-1 expression
JP4129574B2 (ja) * 2002-08-06 2008-08-06 大塚製薬株式会社 老化防止剤
US20040161391A1 (en) * 2002-12-18 2004-08-19 L'oreal Ascorbic acid compounds as bleaching agents
FR2850666B1 (fr) * 2003-01-30 2007-09-07 Oreal Procedes de preparation d'un epiderme reconstruit supplemente en ceramide 7 et/ou 5.5.
US7169382B2 (en) * 2003-01-30 2007-01-30 L'oreal Reconstructed epidermis/skin equivalent comprising a ceramide 7 and /or 5.5 and lipid lamellar vesicular compositions comprising ceramide 7 and/or 5.5 compounds
US20040175347A1 (en) * 2003-03-04 2004-09-09 The Procter & Gamble Company Regulation of mammalian keratinous tissue using hexamidine compositions
JP2009536965A (ja) * 2006-05-15 2009-10-22 ザ プロクター アンド ギャンブル カンパニー 水溶性活性物質の浸透の増強方法
US20070274932A1 (en) * 2006-05-15 2007-11-29 The Procter & Gamble Company Water in oil emulsion compositions containing sunscreen actives and siloxane elastomers
US20090011035A1 (en) * 2007-07-03 2009-01-08 Joseph Michael Zukowski Personal care composition
JP5165299B2 (ja) * 2007-07-20 2013-03-21 ポーラ化成工業株式会社 皮膚外用剤
EP3130332B1 (de) * 2014-04-14 2020-08-26 Hayashibara Co., Ltd. Äusserliches anti-aging-hautpräparat

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US8039026B1 (en) 1997-07-28 2011-10-18 Johnson & Johnson Consumer Companies, Inc Methods for treating skin pigmentation
EP1192938A2 (de) * 2000-09-29 2002-04-03 JOHNSON & JOHNSON CONSUMER COMPANIES, INC. Zusammensetzung zur Verbesserung der Permeation von topischen Hautpflegemitteln
EP1192938A3 (de) * 2000-09-29 2004-01-02 JOHNSON & JOHNSON CONSUMER COMPANIES, INC. Zusammensetzung zur Verbesserung der Permeation von topischen Hautpflegemitteln
FR2825922A1 (fr) * 2001-06-15 2002-12-20 Oreal 2-hexadecanoate d'ascorbyle comme inhibiteur de no-synthase et utilisations
WO2002102343A1 (fr) * 2001-06-15 2002-12-27 L'oreal - D.I.P.I. 2-hexadecanoate d'ascorbyle comme inhibiteur de no-synthase
EP1374850A1 (de) * 2002-06-20 2004-01-02 L'oreal Kosmetische und/oder dermatologische Verwendung einer Zusammensetzung, die mindestens einen oxidationsempfindlichen hydrophilen durch mindestens einem Polymer oder Copolymer stabilisierten Wirkstoff aus Maleinsäureanhydrid enthält
EP1430883A1 (de) * 2002-12-18 2004-06-23 L'oreal Kosmetische Vewendung von Ascorbinsäurederivaten als Haut- oder Haar-Aufheller
FR2848846A1 (fr) * 2002-12-18 2004-06-25 Oreal Utilisation cosmetique de derives de l'acide ascorbique comme agents blanchissants
FR2850579A1 (fr) * 2003-02-03 2004-08-06 Oreal Utilisation de mono-ou di-esters d'acide cinnamique ou de l'un de ses derives et de vitamine c, comme donneur de no
EP1442739A1 (de) * 2003-02-03 2004-08-04 L'oreal Verwendung von Zimtsäure mono- und di-Estern oder von Derivaten und Vitamin C, als NO Donor
EP1620419A2 (de) * 2003-04-21 2006-02-01 Tagra Biiotechnologies Ltd. Stabilisierte ascorbinsäurederivative
EP1620419A4 (de) * 2003-04-21 2008-07-23 Tagra Biotechnologies Ltd Stabilisierte ascorbinsäurederivative
FR2855047A1 (fr) * 2003-05-19 2004-11-26 Oreal Composition comprenant une base sphingoide, un activateur de la voie des 4-et/ou des 6-hydroxylases et un acide gras, utilisation pour renforcer la fonction barriere de la peau
EP1527777A1 (de) * 2003-10-31 2005-05-04 MERCK PATENT GmbH Zubereitung mit antioxidanten Eigenschaften, die einen Benzoesäureester der Ascorbinsäure enthält
EP1842522A4 (de) * 2004-12-28 2015-07-08 Otsuka Pharma Co Ltd Feste öl-in-wasser-emulsion
EP2204163A1 (de) 2008-12-30 2010-07-07 L'oreal Kombination aus Monosaccharide und Ascorbinsäure und ihre kosmetische Verwendung
WO2010142663A1 (fr) * 2009-06-08 2010-12-16 Pierre Fabre Dermo-Cosmetique Mono esters et bis esters d'acide gras insature sur l'acide ascorbique et leurs utilisations cosmetiques
US8722729B2 (en) 2009-06-08 2014-05-13 Pierre Fabre Dermo-Cosmetique Unsaturated fatty acid monoesters and diesters on ascorbic acid and cosmetic uses thereof
WO2013021105A2 (fr) 2011-08-11 2013-02-14 Ascorbix Sarl Nouveaux dérivés de furanones et composition pharmaceutique les contenant

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JP2001316261A (ja) 2001-11-13
US20020042380A1 (en) 2002-04-11
EP1145710B1 (de) 2006-11-02
ATE344016T1 (de) 2006-11-15
DE60124170D1 (de) 2006-12-14
DE60124170T2 (de) 2007-08-30
US20030176366A1 (en) 2003-09-18
FR2807320B1 (fr) 2002-05-24
JP2006070048A (ja) 2006-03-16
FR2807320A1 (fr) 2001-10-12

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